Synthesis of the 8-Deoxy Analogue of 4,9-Anhydro-10-hemiketal-5-deoxy-tetrodotoxin, a Proposed Biosynthetic Precursor of Tetrodotoxin.

Tadachika Miyasaka, Masaatsu Adachi, Toshio Nishikawa

Organic letters 2021 Dec 03

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Despite decades of research, the biosynthesis of tetrodotoxin, also known as a puffer fish toxin, remains an unsolved mystery. We disclose a synthesis of the 8-deoxy analogue of 4,9-anhydro-10-hemiketal-5-deoxy-tetrodotoxin, a possible biosynthetic precursor of tetrodotoxin isolated from the Japanese toxic newt, by an intramolecular radical cyclization of a known starting material.

Citation

Tadachika Miyasaka, Masaatsu Adachi, Toshio Nishikawa. Synthesis of the 8-Deoxy Analogue of 4,9-Anhydro-10-hemiketal-5-deoxy-tetrodotoxin, a Proposed Biosynthetic Precursor of Tetrodotoxin. Organic letters. 2021 Dec 03;23(23):9232-9236